Top Chicago City Tours - page 5

Bike Tour in Chicago

3 hoursFree Cancellation

Turn heads and take in the views with your Premier Chicago Tour Experience! Your journey begins in the passenger seat of an automotive masterpiece. Tour downtown Chicago in an Exotic Sports Car where you'll discover the luxury boutiques of the Magnificent Mile, and enjoy breathtaking waterfront views on Lake Shore Drive. After your scenic tour, enjoy 10 minutes of dedicated photo-op time at the departure point located at the Heart of Downtown Chicago. Whether it’s for social media or a personal keepsake, you’ll have plenty of time to pose with these mechanical works of art against the backdrop of the Windy City before your next adventure begins. More info THE VEHICLES CONSIST OF EXOTIC SPORTS CARS FROM MAKES SUCH AS LAMBORGHINI, FERRARI, MCLAREN, ASTON MARTIN & MORE! Group passenger vehicles consist of Vehicles from make such as Lamborghini, Aston Martin, Rolls-Royce, Bentley & MORE.

Downtown Chicago City Tour in a Super Car [30 Minute Experience]

Your private luxury tour experience begins with a prompt pickup in downtown Chicago. Step inside the climate-controlled cabin of a world-class Rolls-Royce. Your professional chauffeur will navigate the bustling streets of the Windy City. Glance through the panoramic windows at towering skyscrapers like the Willis Tower. Coast down Michigan Avenue to admire the luxury boutiques of the Magnificent Mile. Pass by the architectural marvels of the Loop and the lakefront beauty of Grant Park. This tour itinerary maximizes your time in the city. It is ideal for couples celebrating an anniversary, travelers on a tight schedule, or anyone seeking a VIP Chicago experience. Avoid the crowds of standard tour buses. Enjoy the privacy, comfort, and prestige of DS Luxury Rolls-Royce Tour.

Downtown Chicago City Tour in a Rolls Royce[60 Minute Experience]

This tour offers a refreshing blend of Chicago’s iconic sights and hidden suburban gems, giving travelers a unique perspective on the city's diverse culture, history, and architecture. Start by marveling at Chicago’s world-renowned skyline, exploring its legendary landmarks, and soaking in the vibrant energy of the city. Then, step beyond the usual tourist path to uncover the hidden treasures nestled in the suburbs. Discover the BAPS Shri Swaminarayan Mandir, an architectural masterpiece showcasing intricate carvings and spiritual serenity; visit the quirky Leaning Tower of Niles, a charming replica of Italy’s famous landmark; experience the awe-inspiring Bahá’í House of Worship, known for its breathtaking design and peaceful ambiance; and stroll through Westfield Old Orchard, a stylish open-air shopping destination offering a blend of modern luxury and relaxed charm. This thoughtfully curated journey bridges the gap between city excitement and suburban surprises. Ready to explore?

Chicago City's Iconic Sights and Suburb Gems Tour

5 to 10 hoursFree Cancellation

Price varies by group size

Chicago Private Tour

3 hoursFree Cancellation

Discover the very best of New York City in one unforgettable experience! From the majestic Statue of Liberty and the historic Brooklyn Bridge to famous neighborhoods, hidden gems, and picture-perfect skyline views — this tour captures it all. Enjoy guided stops at iconic landmarks, learn fascinating stories from your local guide, and experience the true energy of the city that never sleeps. Perfect for first-time visitors or anyone wanting to see it all, this experience blends history, culture, and unbeatable photo ops at every turn. Come ready to explore, snap amazing pictures, and make lasting memories on the ultimate NYC adventure!

2 to 7 hoursFree Cancellation

Chicago VIP Private Tour

Discover the charm of Milwaukee on a small group day trip from Chicago! Enjoy a guided city tour, explore iconic landmarks, and experience the legendary Miller Brewery with exclusive behind-the-scenes access and tastings. With comfortable transport, expert local insights, and a friendly group atmosphere, this all-inclusive adventure is perfect for curious travelers. Book now for a memorable escape to Milwaukee's culture and flavors!

Chicago-Milwaukee Small Group Tour

6 to 7 hoursFree Cancellation

Price varies by group size

Six days to enjoy the beautiful scenery of the three major lakes in the Great Lakes region of the United States, all of which are located in Lake Michigan in the United States, Lake Superior, the largest freshwater lake in the world, and Lake Huron. Famous cities along the five great lakes: Chicago, Milwaukee and Traverse City along Lake Michigan, Green Bay along Green Bay, and Sault Ste. Mackinac Island, which was once selected as one of the top ten most beautiful islands in the world. Room Details All hotel rooms are based on two Full / Double beds or one King/Queen bed depends on what rooms are availiable at the hotel on the day. The maximum occupancy per room is four travelers. One Room Selection If you are a party of more than four guests or desire to have separate rooms, please create separate bookings. Avoid traveling in a different bus? If you have more than one booking, please provide all confirmation numbers once your bookings are complete.

Chicago Milwaukee and Lakes 6 Day Tour

6 daysFree Cancellation

Price varies by group size

This tour offers a personalized and stress-free way to experience Chicago, combining comfortable transportation with local insights and flexible stops. Guests enjoy a private ride through iconic neighborhoods and landmarks while learning about the city’s history, culture, and architecture at their own pace. Ideal for airport transfers, short stays, and first-time visitors seeking a relaxed yet memorable city experience

Chicago Exotic Auto Experience

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What are people saying about Chicago

Lake Michigan Skyline Cruise in Chicago

Tess_K, Sep 2026

Captain Bob is the Best!

Info is great but pre-recorded. The route took us out along the breakwater and also ran closer to shore. Captain Bob was open to some questions, once we were docked. Ask him about the lock between the Chicago River and Lake Michigan…critical infrastructure that seems largely unnoticed…

Chicago Favorites Ultimate Food and Walking Tour

Rachel_S, Sep 2026

Amazing!

This was a great experience! Brayden did an amazing job explaining the history of the food and the city itself. He also did a great job keeping us on track. There was more food than is in the description which was a pleasant surprise. It is a lot of walking but it wasn’t bad because of how it was broken up. Probably our favorite excursion while in Chicago…except for seeing the Cubs play.

Lake Michigan Sunset Cruise in Chicago

Summer_M, Sep 2026

Beautiful cruise

Great way to see the city in a different light. We went on the 6pm boat in September, bring a jumper ! It's warm during the day but can get cold at night. A few facts about the buildings at the start were interesting, but the view was just spectacular. A definite must do !

Chicago River 90-Minute Architecture Tour

Judy_H, Sep 2026

So interesting.

The tour guide was very knowledgeable and funny. Devin ( i think that was his name ) I do believe he was co-captain. We just called him captain. While trying to get to where the boat was. We noticed a gentleman with a jacket that said Wendella We told him we were headed there now. He gave us directions. Then of course we 3 very mature ladies were confused again. So he rescued us again. He took us to the boat.Very kind and helpful man. We loved the tour. We just had a hard time ( sometimes ) figuring out which building she was talking about. I would recommend this boat tour to all. The bartender was also pretty cool. I got a fun foo foo drink. It was very good. ❤️

Chicago Crime and Mob Bus Tour

Leslie_P, Sep 2026

It would be a crime to miss this tour!

I have taken several Viator tours, and they NEVER disappoint! The Mob and Crime Tour was no exception! Jay possesses an impressive knowledge on the subject, and the presentation was balanced to provide people with limited knowledge of Chicago history a good foundation in the subject, yet offered plenty of specific, anecdotal, and trivial facts to further inform and educate guests familiar with "the players" and events of crime in Chicago. The pacing of the presentation was excellent, and information was delivered in an entertaining and interesting way. Jay was quite skillful at adjusting the presentation to coincide with sites as the bus was driving by. I appreciated the fact that participants were able to leave the bus at the Biograph Theater to spend a little time rather than just driving by. That was a highlight of the tour! All of my other Viable tours have been walking tours -- this was my first bus tour. The bus was clean and comfortable and the driver did a great job navigating traffic -- way to go, Tommy! Jay & Tommy make a great team, and did their very best to make the tour fun & informative. Thanks to both of you for a great tour! I highly recommend this tour --you won't be sorry!

Chicago's Chinatown Food and Walking Tour

Allison_B, Sep 2026

Do yourself a favor!!!

My bestie and I loved this tour! Our guide, Valerie, was so sweet and passionate about the food. We met so many nice people from group members to shop owners, and every dish was delightful! She even helped me find some Mooncake for me to bring home to my daughter. I highly recommend this tour, and you will be very lucky if you get Valerie as your guide!

Chicago River 45-Minute Architecture Tour from Magnificent Mile

Evelynn_T, Sep 2026

Recommended by locals

I went with my friend in town and boyfriend. I am a southside native and looking for a touristy thing to do in the city. It was 95 degrees out but we still had so much fun. The breeze helped and they sell drinks. Would recommend for anyone looking to learn more about our beautiful city.

Original Chicago Architecture Interiors Tour: Dazzling Interiors

Lisa_K, Aug 2026

Discovering Chicago’s hidden treasures

We really enjoyed this architectural tour which revealed so many hidden gems in the interiors of some of Chicago’s most historic buildings. Spencer was a knowledgeable and entertaining guide who clearly has a passion for Chicago and its history. Would recommend this tour to any one.

Chicago in a Day Walking Tour: Food, History & Architecture

mazndene, Aug 2026

Great tour guide and experience.

Great tour, David our guide was very knowledgeable. He took us to places we never would have looked at but WOW. Food was a real bonus it will fill you up. The popcorn stop was an eye opener who would have thought cheese and caramel would be so tasty 😂. Would definitely recommend this tour Chicago is an amazing city and thanks to David it was such an enjoyable experience.

Chicago Night Crimes Tour by Bus

Wesley_S, Jul 2026

Fascinating Tour!

What an interesting, and fascinating tour. The rich history of Chicago's mob crimes, while off putting to some, makes for a unique tour experience. If you enjoy learning about crime history, or even heard of Al Capone and the beer wars, Dillinger, Nitty, this is the tour for you. The guide was great, plus it's at night so you get to see the downtown at night which is stunning.